Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
  • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P11/00—Drugs for disorders of the respiratory system
  • A61P11/06—Antiasthmatics
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P37/00—Drugs for immunological or allergic disorders
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
  • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
  • C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
  • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
  • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
  • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
  • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
  • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
  • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
  • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
  • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
  • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
  • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
  • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
  • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
  • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
  • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
  • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
  • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Definitions

• the invention also relates to enantiomers of the compounds of the formula I.
• the invention was based on the object, new compounds with valuable Find properties, especially those used in the manufacture of medicines can be used.
• the anti-asthmatic effect can be determined, for example, by the method of T. Olsson, Acta allergologica 26 , 438-447 (1971).
• the compounds also show an inhibitory effect on the formation of TNF (Tumor necrosis factor) and are therefore suitable for the treatment of allergic and inflammatory diseases, autoimmune diseases and transplant rejection reactions. They can also be used to treat memory problems be used.
• TNF Tumor necrosis factor
• the compounds of formula I can be used as active pharmaceutical ingredients in human and Veterinary medicine can be used. They can also be used as intermediates Manufacture of other active pharmaceutical ingredients.
• radicals R 1 , R 2 , R 3 , R 4 , B, Q and L have the meanings given in the formulas I, II, III, IV and V, unless expressly stated otherwise.
• a and A ' is preferably alkyl, more preferably 1 to 5 fluorine and / or Chlorine substituted alkyl.
• alkyl is preferably unbranched and has 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms, preferably 1, 2, 3, 4 or 5 carbon atoms and preferably means Methyl, ethyl, trifluoromethyl, pentafluoroethyl or propyl, further preferably isopropyl, Butyl, isobutyl, sec-butyl or tert-butyl, but also n-pentyl, neo-pentyl or isopentyl.
• Cycloalkyl preferably has 3-7 C atoms and is preferably cyclopropyl and Cyclobutyl, further preferred for cyclopentyl or cyclohexyl, also for Cycloheptyl.
• Methylene cycloalkyl preferably has 4-8 C atoms and preferably represents Methylene cyclopropyl and methylene cyclobutyl, further preferred for Methylencyclopentyl and Methylencyclohexyl, also for Methylencycloheptyl.
• Alkenyl is preferably vinyl, 1- or 2-propenyl, 1-butenyl, isobutenyl, sec-butenyl, further preferred is 1-pentenyl, iso-pentenyl or 1-hexenyl.
• Alkylene is preferably unbranched and preferably means methylene or ethylene, further preferably propylene or butylene.
• Hal is preferably F, Cl or Br, but also I.
• the radicals R 1 and R 2 can be the same or different and are in the 3- or 4-position of the phenyl ring. They mean, for example, independently of one another hydroxy-, -S-CH 3 , -SO-CH 3 , -SO 2 CH 3 , F, Cl, Br or I or together methylenedioxy. However, they are particularly preferably each methoxy, ethoxy, propoxy, cyclopentoxy, or fluorine, difluoro, trifluoromethoxy, 1-fluorine, 2-fluorine, 1,2-difluoro, 2,2-difluoro, 1,2,2-trifluoro or 2,2,2-trifluoroethoxy.
• radicals R 3 and R 4 each independently represent H or A.
• the radical B is preferably 2- or 3-furyl, 2- or 3-thienyl, 1-, 2- or 3-pyrrolyl, 1-, 2-, 4- or 5-imidazolyl, 1-, 3-, 4- or 5-pyrazolyl, 2-, 4- or 5-oxazolyl, 3-, 4- or 5-isoxazolyl, 2-, 4- or 5-thiazolyl, 3-, 4- or 5-isothiazolyl, 2-, 3- or 4-pyridyl, 2-, 4-, 5- or 6-pyrimidinyl, further preferably 1,2,3-triazol-1-, -4- or -5-yl, 1,2,4-triazol-1-, -3- or 5-yl, 1- or 5-tetrazolyl, 1,2,3-oxadiazol-4- or -5-yl, 1,2,4-oxadiazol-3-or -5-yl, 1,3,4-thiadiazol-2- or -5-yl, 1,2,4-thiadiazol-3- or -5-yl, 1,2,3-thiadiazol-4- or -5
• the radical B preferably furthermore denotes methyl, ethyl, propyl, n-butyl, methoxy, Ethoxy, propoxy, N-methylamino, N, N-dimethylamino, N-ethylamino or N, N-diethylamino.
• R 1 , R 2 , R 3 , R 4 and Q have the meanings indicated, in particular the preferred meanings indicated.
• Q is preferably methylene or Ethylene, further preferably for propylene or butylene.
• B has the given preferred in the compounds of the formulas III and V Meanings while L is Cl, Br, OH or a reactive esterified OH group means.
• L represents a reactive esterified OH group
• this is preferred Alkylsulfonyloxy with 1-6 C atoms (preferably methylsulfonyloxy) or arylsulfonyloxy with 6-10 carbon atoms (preferably phenyl or p-tolylsulfonyloxy, also 2-naphthalenesulfonyloxy).
• the starting materials can also be formed in situ, so that they are not isolated from the reaction mixture, but instead are immediately reacted further to give the compounds of the formula I. On the other hand, it is possible to carry out the reaction in stages.
• the compounds of formula I can preferably be obtained by: Reacts compounds of formula II with compounds of formula III.
• the compounds of the formula II are reacted with the Compounds of formula III in the presence or absence of an inert solvent at temperatures between about -20 and about 150 °, preferably between 20 and 100 °.
• Suitable inert solvents are e.g. Hydrocarbons such as hexane, petroleum ether, Benzene, toluene or xylene; chlorinated hydrocarbons such as trichlorethylene, 1,2-dichloroethane, Carbon tetrachloride, chloroform or dichloromethane; Alcohols like Methanol, ethanol, isopropanol, n-propanol, n-butanol or tert-butanol; Ether like Diethyl ether, diisopropyl ether, tetrahydrofuran (THF) or dioxane; Glycol ether like Ethylene glycol monomethyl or monoethyl ether (methyl glycol or ethyl glycol), Ethylene glycol dimethyl ether (diglyme); Ketones such as acetone or butanone; Amides like Acetamide, dimethylacetamide or dimethylformamide (DMF); Nitriles such
• Compounds of the formula I can furthermore be obtained by reacting compounds of the formula IV with compounds of the formula V.
• the starting compounds of the formulas IV and V are generally known. If they are not known, they can be produced by methods known per se. For example, the production of 1-benzoyl-tetrahydropyridazine is described in J. Med. Chem. 38 , 4878 (1995).
• the radical -CO-L means a preactivated one Carboxylic acid, preferably a carboxylic acid halide.
• a base of formula I can with an acid in the associated acid addition salt are transferred, for example by reacting equivalent amounts of the base and the acid in an inert solvent such as ethanol and then evaporating.
• acids that are physiological are suitable for this implementation deliver safe salts.
• So inorganic acids can be used, e.g. Sulfuric acid, nitric acid, hydrohalic acids such as hydrochloric acid or Hydrobromic acid, phosphoric acids such as orthophosphoric acid, sulfamic acid, further organic acids, especially aliphatic, alicyclic, araliphatic, aromatic or heterocyclic mono- or polybasic carboxylic, sulfonic or sulfuric acids, e.g.
• Formic acid acetic acid, propionic acid, pivalic acid, diethyl acetic acid, malonic acid, Succinic acid, pimelic acid, fumaric acid, maleic acid, lactic acid, tartaric acid, Malic acid, citric acid, gluconic acid, ascorbic acid, nicotinic acid, isonicotinic acid, Methane or ethanesulfonic acid, ethanedisulfonic acid, 2-hydroxyethanesulfonic acid, Benzenesulfonic acid, p-toluenesulfonic acid, naphthalene mono- and disulfonic acids, Lauryl sulfuric acid. Salts with physiologically unacceptable acids, e.g. picrates, can be used for the isolation and / or purification of the compounds of formula I. become.
• physiologically unacceptable acids e.g. picrates
• the invention further relates to the use of the compounds of the formula I. and / or their physiologically acceptable salts for the production of pharmaceutical Preparations, in particular by non-chemical means.
• they can work together with at least one solid, liquid and / or semi-liquid carrier or auxiliary and optionally in combination with one or more other active ingredients in one suitable dosage form are brought.
• the invention also relates to compounds of the formula I and their physiological properties harmless salts to combat osteoporosis, tumors, atherosclerosis, rheumatoid arthritis, multiple sclerosis, diabetes mellitus, ulcerative colitis, inflammatory diseases, allergies, asthma, autoimmune diseases, AIDS and Transplant rejection.
• the invention also relates to medicaments of the formula I and their physiological properties harmless salts as phosphodiesterase IV inhibitors.
• the invention furthermore relates to pharmaceutical preparations containing at least one compound of formula I and / or one of its physiological harmless salts.
• the invention further relates to the use of compounds of the formula I. and / or their physiologically acceptable salts for the manufacture of a medicament for combating osteoporosis, tumors, atherosclerosis, rheumatoid arthritis, multiple Sclerosis, diabetes mellitus, ulcerative colitis, inflammatory diseases, allergies, Asthma, autoimmune diseases, AIDS and graft rejection.
• Organic or inorganic substances come in as carriers Question that is suitable for enteral (e.g. oral), parenteral or topical application and do not react with the new compounds, for example water, vegetable oils, Benzyl alcohols, alkylene glycols, polyethylene glycols, glycerol triacetate, gelatin, Carbohydrates such as lactose or starch, magnesium stearate, talc, petroleum jelly.
• Application solutions preferably oily or aqueous solutions, furthermore suspensions, Emulsions or implants, for topical application of ointments, creams or powders.
• the new compounds can also be lyophilized and the resulting lyophilisates e.g. to Manufacture of injectables can be used.
• the specified preparations can be sterilized and / or auxiliary substances such as lubricants, preservatives, stabilizers and / or Wetting agents, emulsifiers, salts to influence the osmotic pressure, Contain buffer substances, color, taste and / or several other active ingredients, e.g. one or more vitamins.
• auxiliary substances such as lubricants, preservatives, stabilizers and / or Wetting agents, emulsifiers, salts to influence the osmotic pressure, Contain buffer substances, color, taste and / or several other active ingredients, e.g. one or more vitamins.
• the compounds of formula I and their physiologically acceptable salts can combating diseases in which an increase in cAMP (cyclo-adenosine monophosphate) level anti-inflammatory leads or prevention and muscle relaxation become.
• cAMP cyclo-adenosine monophosphate
• Particular use can be made of the invention Compounds in the treatment of allergies, asthma, chronic Bronchitis, atopic dermatitis, psoriasis and other skin diseases and find autoimmune diseases.
• a suspension of 4.70 g of 3- (3,4-dimethoxyphenyl) -1,4,5,6-tetrahydropyridazine ("A") in 150 ml of THF is mixed with 2.24 g of potassium tert-butoxide and stirred for 30 minutes.
• 7.3 g of 4-nicotinoylaminobenzoyl chloride are added and stir for 10 hours at room temperature. The solvent is removed and refurbished as usual.
• 1- (4-Nicotinoylamino-benzoyl) -3- (3,4-dimethoxyphenyl) -1,4,5,6-tetrahydro-pyridazine is obtained, Hydrochloride, F. 239 ° (decomposition).
• reaction of 1- (4-aminobenzylcarbonyl) -3 (3,4-dimethoxyphenyl) -1,4,5,6-tetrahydro-pyridazine is obtained with isonicotinoyl chloride 1- (4-isonicotinoylamino-benzylcarbonyl) -3- (3,4-dimethoxyphenyl) -1,4,5,6-tetrahydro-pyridazine, hydrochloride, mp 209 ° and with ethyl chloroformate 1- (4-Ethoxycarbonylamino-benzylcarbonyl) -3- (3,4-dimethoxyphenyl) -1,4,5,6-tetrahydro-pyridazine, mp 143 °.
• Example A Injection glasses
• a solution of 100 g of an active ingredient of the formula I and 5 g of disodium hydrogen phosphate is in 3 l of double distilled water with 2 N hydrochloric acid adjusted to pH 6.5, sterile filtered, filled into injection glasses, lyophilized under sterile conditions and sealed sterile. Every injection jar contains 5 mg of active ingredient.
• a mixture of 20 g of an active ingredient of the formula I is melted with 100 g soy lecithin and 1400 g cocoa butter, pour into molds and let cool. Each suppository contains 20 mg of active ingredient.
• a solution of 1 g of an active ingredient is prepared of the formula I, 9.38 g of NaH 2 PO 4 ⁇ 2 H 2 O, 28.48 g Na 2 HPO 4 ⁇ 12 H 2 O and 0.1 g of benzalkonium chloride in 940 ml of double- distilled water. It is adjusted to pH 6.8, made up to 1 l and sterilized by irradiation. This solution can be used in the form of eye drops.
• Example D ointment
• 500 mg of an active ingredient of the formula I are mixed with 99.5 g of petroleum jelly under aseptic conditions.
• a mixture of 1 kg of active ingredient of the formula I, 4 kg of lactose, 1.2 kg of potato starch, 0.2 kg talc and 0.1 kg magnesium stearate is more common Formed into tablets in such a way that each tablet contains 10 mg of active ingredient contains.
• Example F coated tablets
• Example E Analogously to Example E, tablets are pressed, which are then made in the usual manner Wise with a coating of sucrose, potato starch, talc, tragacanth and dye are coated.
• Example G capsules
• a solution of 1 kg of active ingredient of the formula I in 60 I of double distillation Water is sterile filtered, filled into ampoules, under sterile conditions lyophilized and sealed sterile. Each ampoule contains 10 mg Active ingredient.

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• Life Sciences & Earth Sciences (AREA)
• Public Health (AREA)
• General Chemical & Material Sciences (AREA)
• Medicinal Chemistry (AREA)
• Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
• Chemical Kinetics & Catalysis (AREA)
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